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All listings in Cruz Bay

Great sailboat rentals near Cruz Bay, St. John.

Page 1 of 15 listings

Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$485day
Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick
Sailing in Cruz Bay · 12 guests

Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick

5.0
$125hour
Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. John pick up
Sailing in Cruz Bay · 6 guests

Private Luxury Sailing Day Charter aboard 46ft Catamaran- St. John pick up

New
$325hour
Sail onboard 43' Wooden Yawl "Cimmaron" Classic Sailboat in US Virgin Islands with with Captain Rick!
Sailing in Cruz Bay · 12 guests

Sail onboard 43' Wooden Yawl "Cimmaron" Classic Sailboat in US Virgin Islands with with Captain Rick!

New
$1,000day
Luxury Sailing Experience  – The Ultimate Caribbean Adventure
Sailing in Cruz Bay · 6 guests

Luxury Sailing Experience – The Ultimate Caribbean Adventure

New
$250hour

Sailing Reviews in Cruz Bay

  1. BJ

    Beautiful

    Sailing Cruise Saint John

    Booked with them 3 years ago and still can’t stop thinking of them. I’ve been looking high and low to post my review. Had an amazing time, food was delicious. All above 10/10

  2. RB

    Rose

    Sailing Cruise Saint John

    Book now! This was such a memorable experience! From the line of communication, to Shana amazing Mediterranean platter to captain in training Jaya keeping my son company, it was amazing! From pick up to drop off such a wonderful experience. We cannot wait to see them again this time hopefully in Maine!

  3. HC

    Heather

    Half Day Private Charter in US Virgins Islands onboard 43' Wooden Sailing Yacht "Cimarron" with Captain Rick

    Fabulous day with a knowledgeable captain on a very comfortable boat. Captain Rick customized the trip to our group’s every need and preference. He and his assistant Rachel provided an uniquely memorable Caribbean experience we can highly recommend.

  4. BR

    Bianca

    Sailing Cruise Saint John

    Our family of four spent the entire day sailing, snorkeling, searching for treasures, and swimming at some of most beautiful beaches in the Virgin Islands. Our sons had a blast. The hospitality was top notch and we plan to return!

  5. KF

    Kroll

    Sailing Cruise Saint John

    We had an incredible day of sailing with Shana and her crew! We enjoyed snorkeling in secluded waters, delicious food and drinks, followed by a beautiful sunset sail back to St.John. Thank you for an unforgettable adventure!

  6. TS

    Terri

    Sailing Cruise Saint John

    Absolutely perfect day. Shana and Nicholas were such great hosts. Recommend to anyone looking for a great day on the water.